IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Abstract

(+)-Catechin—laccase oxidation dimeric standards were hemi-synthesized using laccase from Trametes versicolor in a water-ethanol solution at pH 3.6. Eight fractions corresponding to eight potential oxidation dimeric products were detected. The fractions profiles were compared with profiles obtained with two other oxidoreductases: polyphenoloxidase extracted from grapes and laccase from Botrytis cinerea. The profiles were very similar, although some minor differences suggested possible dissimilarities in the reactivity of these enzymes. Five fractions were then isolated and analyzed by 1D and 2D NMR spectroscopy. The addition of traces of cadmium nitrate in the samples solubilized in acetone-d6 led to fully resolved NMR signals of phenolic protons, allowing the unambiguous structural determination of six reaction products, one of the fractions containing two enantiomers. These products were then analyzed in grape seed extracts and red wines (UHPLC-Q-Orbitrap MS). The different dimers had different fragmentation patterns according to their interflavan linkage position. Oxidation dimeric compounds had a specific fragment ion at m/z 393, missing for B-Type dimers fragmentations. A fragment ion at m/z 291 occurred and was specific for oxidation dimeric compounds with a C-O-C linkage. Higher level oxidation products had abundant specific fragments: m/z 425, 397 and 245. These fragmentations were useful to identify them in complex samples such as grape seed extracts and wines. Three grape varieties and three ripening stages were selected and the corresponding seed extracts were obtained. The analyses revealed an increasing trend for the oxidation markers during grape ripening. The analysis of Syrah wines (2018, 2014, 2010) showed a decreasing trend of these molecules during wine ageing which might be due to further oxidation.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Saucier Cedric1, Deshaies Stacy1, Le Guernevé Christine1,2, Sommerer Nicolas1,2, Garcia Lucas Suc François1, Mouls Laetitia1

1SPO, Université de Montpellier, INRAE, Institut Agro, UMR SPO, Faculté de Pharmacie, 15 avenue Charles Flahault, 34000 Montpellier, France
2INRAE, PROBE Research Infrastructure, PFP Polyphenol Facility, 34060 Montpellier, France

Contact the author

Keywords

wine, grape, polyphenol,oxidation, catechin

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Agronomical assessment of a vine « terroir » map: first results in the « AOC » Minervois region

Minervois is a vine region where the first detailed soil map was begun 30 years ago. In 2003, a new map was drawn plotting the soil-landscape associations. This map distinguishes 8 large soil units based on geology. The widest (called « marnes ») is the most complex : it is made of 57 sub-units, which leads to a high variability of the vine behaviour on this unit.

Read More

100 ans d’évolution des règles relatives à l’encépagement des AOC viticoles françaises : quelles perspectives face aux enjeux contemporains

To characterize a wine, the most frequently used criteria describe its color, its origin, the grape varieties from which they come, or even for white wines its residual sugar content (dry, semi-dry, sweet). In france, the system of appellations of origin set up in 1919 was initially based solely on the notoriety and origin of the wines. But given the unfavorable consequences that this lack of details generated, the public authorities quickly integrated in 1927 into the “capus” law criteria for access to designations of origin, relating to the specific characteristics of the soils of the vineyards and the grape varieties used, in particular exclusion of interspecific hybrid varieties. In 1935 the creation of the aoc system confirmed the interest in precisely defining all the production conditions that must be implemented to be able to claim the benefit of an aoc, and grape varieties were an essential condition for acquisition.

Read More

Development of novel drought-tolerant grape cultivars from Monastrell: enhancing anthocyanin and flavonol content under elevated temperatures

The ongoing challenge of climate change is driving the need for novel oenological approaches aimed at finding effective environmental solutions.

Read More

Recherche de relations entre terroir et caractéristiques sensorielles des eaux-de-vie de Cognac

[lwp_divi_breadcrumbs home_text="IVES" use_before_icon="on" before_icon="||divi||400" module_id="publication-ariane" _builder_version="4.19.4" _module_preset="default" module_text_align="center" module_font_size="16px" text_orientation="center"...
Read More

Rootstock influence on xylem embolized vulnerability and scion behavior under severe water deficit

Severe water stress events can induce cavitation damage by xylem embolism in grapevine, diminishing plant hydraulic conductance. This work aimed to determine the rootstock effects on 1) xylem embolism vulnerability to understand its function failure under severe drought, including segmentation processes from leaf to root; and 2) hydraulic conductance across water deficit and its recovery. For this purpose, two complementary experiments were performed in one-year-old Vitis vinifera cv. Tempranillo grafted onto two different rootstocks (110-Richter and SO4) under well-watered 12L pot conditions. In experiment 1, the water-stress induced xylem embolism was monitored in leaves and stems, above and below grafting-point, by using “Cavicam” for determining the percentage of embolized vessels (at P12, P50 and P88).

Read More